Remember the first time you saw the “Purple Swag” video? It felt like something special, like some trailer to a movie that you suddenly realized you have to go see. When it went viral, the video acted as a point of introduction for hundreds of thousands of viewers (now over 12 million) and brought up a lot of questions: What’s the white girl doing with those gold fronts? Why is this New York dude rapping like that? Who is this guy?

Fast forward to now, and we should all be pretty familiar with A$AP Rocky. Nobody’s calling him hip-hop’s savior, but it’s hard to argue that he’s not on a hot streak. He gets by more on style and charisma than skill or depth, but he sounds good doing it and chances are if you like one of his songs you’ll like most of them. This isn’t to say that all his songs are the same—they’re not—but he understands the aesthetic he’s going for and he’s already mastered how to reproduce that aesthetic with everything he touches. It’s this kind of consistency that makes a guy like A$AP Rocky able to brand himself, and it’s the reason you see kids from cities and suburbs across the country with Twitter handles like @asvpxalexander and @DatPrtyMthrFvckr. He’s created something strong enough and distinct enough that people want to be associated with it.

A$AP Rocky, and the people around A$AP Rocky (most notably A$AP Yams, who handpicks beats for Rocky and seems to be somewhat of a mastermind) know what they’re doing. They know that to go big in 2012, you’ve got to sell more than music and the team has always done that well. Along the way they’ve made all the right decisions: working with producers like Clams Casino and Beautiful Lou, teaming up with Blvck Scvle, making sure music videos were effective and on point, and collaborating with all the right people.

They haven’t watered  down their brand. Not yet.

Yesterday, Rihanna released her “Cockiness” remix, featuring none other than A$AP Rocky himself, and for the first time he seemed slightly out of place. It’s weird to say that, because the New York rapper has more Southern flavor than a lot of Southern rappers, sometimes adapts a Bone Thugs flow, and inarguably leans more towards a Pac character than a Biggie. But for the first time, A$AP doesn’t stick to the script that the A$AP guys have been selling up to this point. To top it off, the remix came with the news that A$AP may be joining Rihanna on stage at the 2012 MTV Video Music Awards. This isn’t another well-executed step in the right direction—this is a power move. In a business sense, a sense that Rocky and the rest of the A$AP Mob clearly have, it’s a progression.

The thing is, the career path of A$AP Rocky is getting to that sometimes inevitable point where star power starts to cast a shadow on intrigue. Some early adaptors—the ones often responsible for hyping up new buzzing acts in the first place—lose interest. But for every one of them, the tide brings in a mass of new fans like a swelling pool of red tide that proves toxic to previous inhabitants. We saw it on the horizon; Rocky has come a long way since “Purple Swag” and his earlier work still referenced by hardcore fans. But is this a point of no return, or can A$AP balance the power moves with staying true to what won over his fan base in the first place?

This isn’t an unfamiliar situation to be in, especially for rappers. We’ve seen acts like Wiz Khalifa, Wale, and Big Sean all face some difficulty in keeping those initial fans happy while reaching for a larger audience and sacrificing a little individuality in order to conform for the masses. It’s never an easy task, and there’s no doubt we’ll see it come up again (like when Kendrick Lamar collaborates with Lady Gaga), but this new batch of artists seems particularly savvy. Even under the pressure of major labels, these guys know what made them blow up in the first place, and they strive to keep that alive. It’s this kind of awareness that keeps artists striving not just for popularity, but for artistic integrity (even if it takes an album or two to find it). It’s the kind of thing that separates Drake from Flo Rida, no matter how blurry that distinction is to you.

However you look at it, A$AP Rocky teaming up with Rihanna is a game-changer. There’s a chance that we’ll look back in a year and say, “Yeah, that was the point it all started to go downhill,” and there’s a chance that this will be a spike in the charts that further separates Rocky from the pack of newcomers. It will probably all depend on who you ask. Most importantly, it will depend on what this rising talent decides to do next.

A$AP Rocky’s major label debut, LongLiveA$AP, comes out on Sony this Halloween.